Organic mercury compounds



a'ts

This invention deals with new organic compounds of mercury, useful as fungicides and bactericides for nontherapeutic uses in the preservation of materials other than foods, and the like. These novel compounds comprise condensation products of aliphatic substituted unsaturated hydrocarbons containing a labile negative group, said unsaturated compounds reacting with a divalent inorganic mercury compound, and with a compound containing at least one active hydrogen atom attached to a non-acid polar atom.

Freidlina, Nesmeyanov and Tokareva in Berichte, 698, 20l921 (19'36), mention that hydrobromic acid completely destroys HO-C H -HgCH Br. They, furthermore, state that ethylene dibromide will not form an organic compound with mercury. Also, Whitmores Organic Compounds of Mercury (1921), p. 32, states that, although ethylene forms an organic compound with a mercury salt in the presence of water or alcohol, the addition of alkyl halide or hydrochloric acid yields a quantitative amount of ethylene by decomposition of the product. Such statements no doubt have discour aged many investigators against trying out reactions of this type with the purpose of producing high yields of relative- 1y stable products. In the novel reactions discussed herein, it has been considered surprising that the addition of hydrochloric or other inorganic acid does not decompose the products formed, but merely forms the salt of the acid.

Also, it has been discovered that organic halides, instead of decomposing the reaction product, actually enter the reaction to form fairly stable organic compounds. Formation of thioethers through use of reagents such as 2-mercaptoethanol in the reaction medium of the present invention also is surprising in that it is well-known that inorganic and organic mercury salts react readily with SH groups to form the highly insoluble sulfur products or to reduce the organic compound to metallic mercury.

According to the present invention, allyl chloride, for example, may be reacted with mercuric oxide in the presg ence of acetic acid and methyl alcohol to produce 3- chloro-2-methoxypropyl-mercuric acetate in an essential 1y quantitative yield. Similarly, propargyl chloride may be substituted for allyl chloride, stearic acid for acetic acid, and ethylene glycol for methyl alcohol, to produce high yields of sym.-ethylene bis (3 chloro 2-oxy-propenyl mercuric stearate).

Similarly, .ercuric malonate, allyl isothiocyanate and isopropyl alcohol may be reacted to produce the compound designated as:

Likewise, mercuric oxide, acetic acid, propargyl chloride and diethanolamine may be reacted to form:

tet

which, when reacted with hydrochloric acid, forms the organo-mercuric chloride hydrochloride.

Also, the mercuric salt of monoethyl phosphate, 2- chloroethylvinyl ether and ethyl-Z-mercaptoacetate may be combined to form:

Further, mercuric trichloracetate, methallyl thiocyamate and phosphine, may be reacted similarly to produce a disubstituted phosphine:

And, mercuric oxide, sodium terephthalate (hemi salt), allyl isocyanate and dimethyl arsine may be reacted to yield:

The aliphatic unsaturated hydrocarbons forming one of the reacting ingredients in the formation of the present novel compounds must contain a labile substituent group, such as halogen. For example, as pointed out by Bernthsen in his Textbook of Organic Chemistry, Sudborough Edition, D. Van Nostrand Co., 1927, page 58, halogen substituents, e.g., chlorine, bromine, iodine and fluorine, are labile or readily-replaceable groups. Cther such groups found suitable for the purposes of the present invention are SCN, CNS, ()CN and CNS groups. Although one such labile group is generally used, more than one, and up to twenty of such groups may be employed. The aforesaid reacting compound may contain other substituents, such as other halogens, ether linkages, and the like, which do not enter into the reaction involved herein, and provided such groups do not interfere with the aforesaid reaction by steric hindrance, excessive weakening of the unsaturated bond, or otherwise. Compounds of this type found suitable for this purpose in the reaction set forth herein include allyl chloride, propargyl bromide, oleyl iodide, allyl thiocyanate, allyl isothiocyanate, and the like. It is preferred that such unsaturated reactants have 2 to 30 carbon atoms per molecule, although the most desirable ones at the pres ent time have 2 to 10 carbon atoms per molecule. These latter compounds may be straight chain or branched, provided the unsaturation is in reactive form.

The next ingredient in the novel reaction of the present invention is a divalent mercury compound carrying anions, such as mercuric acetate, mercuric stearate, mercuric bromide, mercuric chloride, mercuric hydroxyacetate, mercuric propionate, and the like. These mercury compounds may be formed in situ during the reaction, by use of mercuric oxide (HgO), using the appropriate anion-forming acid, such as acetic, propionic, hydroxy acetic, and like acid, it being understood that the acid employed would not make the mercury unreactive or too slowly reactive for the purpose of the present invention. The in situ formation of the mercury compound is often more preferable as it aids in controlling the extent of the reaction, as will be hereinafter explained.

oxygen,uand/or sulphur. The term non-acid signifies that the atom must not come from the acid portion of a molecule, such as the oxygen carrying the hydrogen in the radicalCOOH. As pointed out by Whitmore in his Organic Chemistry, Van Nostrand, 1937, page 517, such active hydrogen compounds include water, and alcohols. Other such suitable compounds for the present reaction include mercaptans. Suitable compounds of this type include methanol, ethanol, propanols, chlorethanol, hydroxyacetic acid, ethylene glycol, sorbitol, triethanolamine, diethanolamine, monethanolamine, pentaerythritol, glycerol, 2-amino-2-ethyl-3-propanediol, acetone (enol form), amines sold under the Ethomeen brand, exemplified by C H NH(C H O) C H OH, heptyl mercaptan, high molecular Weight condensates of dehydroabietylamine with ethylene oxide, such as wherein R may be an alkyl group, high molecular Weight polyhydroxy ether compounds, and the like. In the event more than one active hydrogen atom are present in the compound reacting, it is not necessary that all of the active hydrogens enter into reaction, unless this is desired.

The novel compounds produced by this reaction may be classified generically according to the formula:

where R represents the residue of the active-hydrogen compound, other than a bare compound, remaining in the novel compound after the reaction minus the element .to which the active-hydrogen was attached, E represents the non-acidic polar element to which the active hydrogen was attached, A represents the anion, Hg represents mercury, X represents the labile negative group attached to R, R represents a hydrocarbon group having 2 to 30' carbon atoms, a is an integer ranging from one to twice the maximum reacting valence of A, b represents an integer ranging from 1 to 100, represents the ratio ob-i tained by dividing b by the reacting valence of A, and d represents an integer ranging from 1 to 20.

The integer a may have a value up to twice the maximum reacting valence of A. For example, when is employed as a reactant, R becomes CH and thus there are two CH residues present. The termfmaxi mum reacting valence of A employed herein designates the highest valence attainable by A. If the reacting valence of A were 1, then a would have a value of 2. I If the reacting valence of A were 2, then a would have a value of 4, since two distinct monovalent organo-mercuric moieties would be required to satisfy A, and two Rs would be required for each of the two moieties. For example, in Table 1, Example 41, b has a value of 2, and the reacting valence of S0 is 2. Hence c is the ratio of the two and Would have the value of 1. However, in Example 32, b has the value of 2 and the reacting valence of is 1. The ratio of both would give a value of 2 to c; Also, in Example 230, where b has a value of 4 and A has a value oi 1, 0 would have a value of 4. This may be further exemplified, using a compound in which R is the pentaerythritol residue with a reaction capacity which would give a value of 4 for b (as in Example 23c). If the acetate ion is replaced by the phosphate ion, and all available reacting valencies entered the reaction, b would endured-earns In the ease of the allyl chloride-methanol-mercuric acetate reaction already discussed, the reaction may be written as follows:

Using the previously indicated symbols, the reaction product may be designated as:

RXHgA l-R In the case of the complete reaction of allyl chloride,

2-mercaptoethanol and mercuric acetate, for example, the reaction product would be:

Thus, if we use the letter E to designate oxygen or sulfur to which the reacting reactive-hydrogen atom is attached in the active-hydrogen compound, then WQ can 2 u employ the following formula to designate compounds of the present inevntion:

a-( )b c wherein:

E represents a non-acid polar atom selected from the class consisting of oxygen, sulfur, and oxygen and sulfur,

X represents a labile negative substituent selected from the class consisting of halogen, SCN, CNS, OCN and CNO,

R represents the residual moiety of the active-hydrogen compound, less E and its reacted active-hydrogen atom,

R represents a hydrocarbon group having 2 to 30 carbon atoms, and carrying labile substituent X,

Hg represents a mercury atom,

A represents an anion salt portion attached to the mercury atom,

represents the ratio obtained by dividing the number of reacting Es in the compound by the valence of A,

a represents the ratio obtained by dividing the number of reacting active-hydrogen atoms of the active-hydrogen compound by c,

12 represents the number of reacting Es, and is an integer ranging from 1 to 100, and

d represents an integer ranging from 1 to 20.

These novel compounds may be produced simply by mixing a substituted unsaturated hydrocarbon compound with a mercuric salt or with mercuric oxide and an acid corresponding to the salt in the presence of the desired active hydrogen compound, which latter also may be employed in excess as the reaction solvent. There is usually a liberation of heat during the stirring operation, after which the product may be recovered by precipitation, evaporation of the solvent, or by drying from the frozen state. The products formed vary from highly volatile to relatively non-volatile liquids and crystalline or amorphous solids. When using mercuric chloride and other mercury salts which tend to react slowly or incompletely, reaction may be speeded up or brought to completion by occasional addition of alkali or alkaline buffers which maintain an optimum pH range.

As stated previously, although R has been specified as a hydrocarbon group, it is to be understood that this group may contain one or more substituents which do not enter into the reaction of the preesnt invention and which do not interfere with said reaction by steric hindrance, excessive weakening of the unsaturated bond of the reacting parent substituted unsaturated hydrocarbon, or other wise. Such substituents may include halogens, etherlinked groups, nitro groups, as well as other known groups.

From the foregoing, it is apparent that when polyh droxy and/or polysulfhydrated compounds are employed as the active hydrogen compounds, they may be added in less than molar ratios to provide products containing more than one organic mercury moiety linked to the active hydrogen compound residue. In the case of the use of acids such as hydroxyacetic acid, the acid may serve the purpose of being both the active hydrogen compound and the anion.

This invention may be more readily understood by reference to the following examples which depict many phases of the present invention:

EXAMPLE 1 Two moles of allyl chloride, one mole of ethylene glycol, two moles of mercuric oxide and two moles of acetic acid were reacted by adding the mercuric oxide slowly with stirring to the mixture of other compounds in excess acetic acid as solvent.

After 30 minutes (when all mercuric oxide was consumed) the reaction mass was warmed and stirred until no inorganic mercury ions were detectable by the addition of a small test portion to dilute NaOH solution.

6 The resulting product was found to have the empirical formula C H O Hg Cl and was obtained in substantially quantitative yield after stripping ofi of the solvent. It was identified as:

O Cl--CHz-lH-CHrHg-O O 0 CH3 EXAMPLE 2 CHrCHz Cl--CH2--( 3HCI-Iz-Hg-Ol EXAMPLE 3 Three moles of allyl chloride, one mole of triethanolamine, three moles of mercuric oxide and tour moles of acetic acid were reacted as in Example 2 and the chloride salt was formed in the same manner. The react-ion product was found to have the empirical formula EXAMPLE 4 Four moles of allyl chloride, one mole of pentaerythritol, four moles of mercuric oxide and four moles of acetic acid were reacted as in Example 1 to form one mole of an organic mercury compound containing four chloropropyl mercuric acetate moieties connected with each other through the four active hydroxyl hydrogens of the pentaerythritol. The compound had the empirical formula C H O Hg C1 EXAMPLE 5 One mole of allyl isothiocyanate, one mole of methyl alcohol, one mole of mercuric oxide and one mole of acetic acid were reacted as in Example 1, but using an excess of methanol as the reaction solvent. The product obtained was found to be 3-isothiocyano-2-methoxypropyl mercuric acetate having the empirical formula C H O HgNS.

EXAMPLE 6 One mole of allyl thiocyanate, one mole of methanol, one mole of mercuric oxide, and one mole of acetic acid were reacted as in Example 5 to yield S-thiocyano- .Z-methoxy-propyl mercuric acetate having the empirical formula C H O HgNS.

TABLE L-Continued Percent Biological mercury activity Ratio Percent Ex. Reacting comto activity No. ponents Compound formed Empirical formula MW correover spondthat of Cale. Fd. lug PMA phenyl basis Hg mersalt cury content 6:: Ally] chloride, C1-CH2--CHCHg-Hg-Cl CIRHIHHEQNCIA- 771 52. 4 52. 2 0. 96 8. 4

mercuric chloride, sodium CHzOHz hydroxide, triethanolamine. N""G2H4OH 0 CHzCHz ClCHzCH--CHz-Hg-Cl 0b.-. Allyl chloride, Triple substitution u 270: EsNC1a.- 1, 084 55. 55. 4 1.00 o. o

mercuric chloride, sodium hydroxide, triethanolamiue.

7.-. Allyl chloride. Cl-CH-OH-OH Hg-O O CCH; CzaHn01HgCl.- 731 27. 3 27.3 0.58 21.2

mercuric oxide, acetic acid, nonylphenoxy (CzH40)4 OaHn triethoxy ethanol.

8. Allyl chloride, OlCH -CHCH -Hg0 O C CH: 11 21 g 4 44- 3 44.1 0- 83 1 4 mercuric oxide, acetic acid, 0 021140 01H 2-butoxy ethanol.

9- Allyl chloride, ClCHrCHCHa-Hg0 0 O OH; CHH2306 gC1 483 41. 5 41. 5 0.84 17. 2

mercuric oxide, acetic acid, CSHflO osmo CH: monomethyl ether of dipropylene glycol.

Allyl chloride, C1CHr CH-CHzHgO O C CH; C1oHnO4HgCl. 437 45. 9 45. 8 0. 79 2. 6

mercuric oxide, acetic acid, C1120 04H? tetrahydrofurfuryl alcohol.

11.. Ally] chloride, Cl-CH -CHCH2Hg-O O O OH: i9Hi19 i23- 973 5 6 41 5- 8 mercuric oxide, acetic acid, I nouylphenoxy O C2H4( 0 Q 114) m 0 polyethoxy ethanol. CoHm 12 Allyl chloride, C1-'-CH2OH-CH2HgO O C CH; C44Hsi0mHg0l... 1,107 18.1 18.0 0. 24. 0

mercuric oxide, acetic acid, CaHa(O 03110110 CaH OH polypropylene glycol.

12a, Allyl chloride, C1CHg-CH-CHzHgOOCCH3 O4vHe40isHgzClz. 1, 442 27.8 27.6 0.52 10.4

mercuric oxide, acetic acid, C3He(0 CiHehiO CcHeO polypropylene glycol.

C1-CH2 OHCH2-Hg0 O C CH:

13. Allyl chloride, OlOHCHOH:-Hg-O O C CH; CiaH2a0iHECl. 481 41. 7 41. 6 0. 77 9.1

mercuric oxide. acetic acid, 3-hydroxy-2- OCH5CHCH 01103111 ethylhexanol.

13c Allyl chloride, C1OH2CHOHz-Hg0 O O OH; O1sH320aHgzCh. 816 49. 2 49. 0 0. 80 4.0

mercuric oxide, acetic acid 3- C211 hydroxy 2 ethylhexcuol. O-CHz-CHOH-C H1 ClCHz--CHCH Hg-O O 0 01-12 14. Allyl chloride, C1-OH2GH0H HgO O O OH: C11+Haa+0s+HgOl 1 620 32. 3 32. 0 0. 64 15. 3

mercuric acetate acetic O (C2H40)5+C2H4OH acid, polyethylene glycol.

14a Ally] chloride, C1-CH:CHCHz-Hg0 OCCH; z2+ 4e|-0u+ E2 h 6 1 41.8 42-0 0-85 17.5

mercuric acetate, acetic (C2H40)5+GZH1O acid, polyethylene glycol.

Ol-CH2CHCHaHg-O 0 O CH:

TABLE IContinued Percent Biological mercury activity Ratio Percent Ex, Reactingcomto activity ponnts Compound formed Empirical formula MW correover spondthat of Calc. Fd. ing PMA phenyl basis Hg mersalt cury content 15 Allyl chloride, (ll-CHg-CBF-CH -Hg-O O C CH3 CnHnoiHgCl 425 47. 2 i 47. 0. 90 12.1

mercuric acetate, mono- C2H4O CzHu ethyl ether of ethylene glycol Allyl chloride, ClCHzOHOHiHg-0 00 CH: cumtosn ci-.." 489 41; 0 41.0 0. 82 16.1

mercuric acetate, CioHn a-terpineol.

17, Allyl chloride, ClCHr-CH--CH;|Hg-O 0 C CH oumiomgmol. 499 40. 2 40.1 0.70 3. 5

mercuric oxide, 1 acetic acid CiH4NHCaH4NH HAc hydroxyethyl ethylene H O O C CH: diamine.

13 Allyl chloride, Cl-OHz-CH-CHr-Hg-O O CH CoHm0lHgNC1.. 440 45. 6 45. 6 l 0.88 12.8

mercuric oxide, acetic acid, CgHiNH C2H4OH diethanolamlue.

- H O C CHa 13 allyl chloride, OlCH CHCH2-Hg-0 O C CH: C -H' OcHgiNCIL. 775 51'. 9 51. 8 0.96 9, 4

mercuric oxide, acetic acid, CgH4-NHHO 0 C CH: diethanolamine.

O-G2Ha ClCH-( H-CHr-Hg0 0 O OH:

19 Allyl chloride, OlCH5CHCHg-Hg-Cl CUHMOQHENCH" 541 37. 1 37. 1 0.65 4. 2

mercuric chloride, sodium (CaH40)aCzH4NH2H Gl hydroxide, amino poly ethylene glycol.

20 Allyl chloride. ClCHrCH-CHi-Hg0 O CH: 01H,,0=H Nc1-- 392 51. 2 51. 2 1.06 18.8

mercuric oxide, acetic acid, CHQCN glycolonitrile.

21- Allyl chl e, C1CH:CHCHz-Hg 0 0 H: zvHasOoHgNCl.-- 800 25.1 25. 0 0.58 27. 4

mercuric oxide, acetic acid. (O:H)4C2H4NH(CH2)1ICHS Ethomeen 0-15 (Armour). HAc 22 Allyl chloride, Cl-OHz-CH-CHg-Hg-O 0 C CH: CcH aO4HgC17.. 460 43. 6 43. 6 0. 73 0 mercuric oxide, acetic acid, 021140 GzHiCl diethylene glycol, chlorohydrin.

23, Allyl chloride. Cl-CHi--OHCHHgO 0 0 OH: C HinmHgCl.-. 471 42. 6 42. 0 0. 71 -0. 4

mercuric oxide, acetic acid, CHzC (CHaOH): pentaerythritol.

23a Allyl chloride, C1-CH:CHCHz-Hg-O O C CH: 0 5 0 11901.-. 806 49. 8 49. 7 0. 92 9. 25

mercuric oxide, acetic acid. CH; pentaerythritol.

C1--CHz-GHCH:Hg-O O C CH;

2312.. Allyl chloride, Triple substitution CruHaaOmHgsClz... 1, 141 52. 8 52. 6 1. 26 29 3 mercuric oxide, acetic acid, pentaerythritol.

230.. Allyl chloride, Quadruple substitution CmHlcOmHgflh... 476 54. 4 54. 4 1. 25 27. o

mercuric oxide, acetic acid, pentaerythritol.

24. Allyl chloride, C1-CHr-CHCH:Hg-O O C CHQCH! C 10H1905HgCL.--- 455 44. 1 4.4. 0 0. 78 5. 2

mercuric oxide, propionic acid, CzH4O OzHiOH diethylene glycol.

24a. Ally] chloride, G1CHa-CHCHi-HgO O C CHQCHQ C1sHzaO7HgnCh.... 804 49. 9 50. 0 0. 11. 9

mercuric oxide, 6 propionic acid, CaH4O C HiO diethylene glycol. Cl-OHg-CH-CHg-Hg-OOO CH CK;

arr/ease TABLE I-Coutinued Ex. No.

Reacting components Compound formed Empirical formula Percent mercury Biological activity Cale.

Ratio to spondth l Y Hg salt Percent activity over at oi PlvL-k basis mercur-y content Allyl chloridc,

mercuric oxide, propionic acid, tridecyl alcohol.

Allyl chloride,

mercuric oxide, propionic acid, lactonitrile.

Allyl chloride,

mercuric oxide, propionic acid, Z-mcrcaptoethanol.

Allyl chloride,

mercuric oxide, propionic acid, 2-mercaptoethanol.

Allyl chloride,

mercuric oxide, propionic acid, Z-ctliyl hexauol.

Allyl chloride,

mercuric oxide, propionic acid, tris (hydroxymethyl) nitromethane.

Allyl isothiocyanate, mercuric oxide, acetic acid, methanol.

Mcthallyl chloride, mercuric oxide, acetic acid, methanol.

2-chlorocthylvinyl ether, mercuric oxide, acetic acid, methanol.

Vinylidene chloride, mercuric oxide, acetic acid, methanol.

Vinyl chloride,

mercuric oxide, acetic acid, methanol.

Vinyl bromide,

mercuric oxide, acetic acid, methanol.

Allyl thiocyanate,

mercuric oxide, acetic acid, methanol.

Olcyl chloride,

mercuric oxide, acetic acid, methanol.

, Ally! iodide,

mercuric acetate, nonoic acid, methanol.

Allyl chloride,

mercuric oxide, phosphoric acid, methanol.

Allyl chloride,

mercuric oxide,

. phosphoric acid, methanol.

Triple substitution-P 04 CcHu03HgNCl CroHrsWHgNCl.-.

C7H O4HgCl ceHeoaHgcl CrgHflOaHEI aHmOrHgP CL-..

1. An organic compound reaction product of a mercuric anionic salt, an active-hydrogen compound, and an aliphatic hydrocarbon having an unsaturated bond and at least one labile substituent group, and having the formula:

a( g)b o wherein:

E represents a non-acid polar atom selected from the class consisting of oxygen, sulfur, and oxygen and sulfur,

X represents a labile negative substituent selected from the class consisting of halogen, SCN, CNS, OCN and CNO,

R represents the residual moiety of the active-hydrogen compound after removal of E and its reacted activehydrogen atom,

R represents a hydrocarbon group having 2 to carbon atoms, and carrying labile substituent X,

Hg represents a mercury atom,

A represents an anion salt portion attached to the mercury atom,

TABLE I-Continued Percent Biological mercury activity Ratio Percent Ex. Reacting com, to activity No. ponents Compound formed Empirical formula MW correover spondthat of Cale. Fd. ing PMA phenyl basis Hg mersalt cury content 41-. Allylchlqride, C1-CH CH-CHzHgS O4 C|H1606Hg7SClI.-- 712 56.3 56.1 1.28 26.2

mercuric. acetate, sulfuric O CH; acid, methanol.

42-- Allylichloride, .Cl.CHq-CH--GHz-.-Hg-H:BO= C4H1n04HgBCL... 369 54.4 54.3 1.28 28.8

mercuric acetate, boric CH3 acid, methanol.

.43-- Allyl chloride, C'lOH .CHCH'H'g QsHrn0zHgzSC1-.. 612 65.5 65.1 1.28 14.5

mercurlc acetate, sodium CH3 8 sulfide, methanol. ClCHzCHCHr- 44-. Ally! chloride, OlCHrCHCHt- Hg-0OCCH= CQH OaHgClHHU 393 61.0 49.9 1.30 32.4

megcuriegxide, ace 10 am acetone. (jJ figssutmed CH2; s rue ure A ly c ClOHrCHCH -Hg00COH: CsH;40:HgCl 394 51.0 50.9 1.30 32.4

mercuric oxide, acetic acid, isopropanol.

46.. Allylisotbiocya- SCNCHz-CHCHzHg.-O O c rnaotngrsrmu 819 48.9 50.0 1.31 36.3

nate,mercurie acetate, malonic 0 acid, isopro- I panol. OHx-CHCH: /CH:

47.. Allylisoeyanate, C H OsHgNASNa 586 34.2 34.1 0.72 19.5

mercuric ace- 0 CN-CHzCHCHzHg-O O C C O ONe tate, sodium 1 terepht-halate CHaAs-CH:

(hemi salt) dimethyl arsine.

48-. Perchlorododecyl OCH; Cr1 r40rHgCl2o..-- 1,193 16.5 16.3 0.43 27.3 vinyl ether, mercuric oxide, H-OCH -Hg-0 O O CH: acetic acid, methanol. C12H&Cl20

1 Ca. I claim: c represents [the ratio obtained by dividing the num- :ber of reacting Es by the valence of A,

a represents the ratio obtained by dividing the-number of reacting active-hydrogen atoms of the activehydrogen compound by c,

b represents the number of reacting Es, and is an integer ranging from 1 to 100, and

d represents an integer ranging from 1 to 20.

2. An organic reaction product according to claim 1 in which R is derived from an organic mercaptan compound.

3. An organic reaction, product according to claim 1 in which R is derived from an alcohol.

4. An organic reaction product according to claim 1 in which X is a halogen.

5. -An organic reaction product according to claim 1 in which R is a propylene group.

References Cited in the file of this patent UNITED STATES PATENTS 1,457,675 Schoeller IuneS, 1923 2,284,067 Ralston et al May 26, 1942 2,289,590 Ralston et a1. July 14, 1942 

1. AN ORGANIC COMPOUND REACTION PRODUCT OF A MERCURIC ANIONIC SALT, AN ACTIVE-HYDROGEN COMPOUND, AND AN ALPHATIC HYDROCARBON HAVING AN UNSATURATED BOND AND AT LEAST ONE LABILE SUBSTITUENT GROUP, AND HAVING THE FORMULA: 